Iodine → HCID 22408234, compound

Participants

Reaction Steps

To a solution of 4-bromobenzaldehyde ethylene acetal (1.5 g, 6.5 millimol) in tetrahydrofuran (7 ml) were added magnesium (170 mg, 7 millimol) and a small amount of iodine, and the mixture was vigorously stirred under nitrogen atmosphere. After most of magnesium was dissolved, the solution was added to a solution of 3-met hoxybenzyltosylate (1.46 g, 5 millimol) and copper(I) bromidedimethylsulfide complex (50 mg, 0.25 millimol) in benzene (14 ml). The mixture was stirred at room temperature for 22 hours. Next, saturated ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. the organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure, The residue was separated and purified by using a silica-gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (850 mg, 3.14 millimol, 63%).

Provenance & Evidence